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US-12617895-B2 - Resin composition and article made therefrom

US12617895B2US 12617895 B2US12617895 B2US 12617895B2US-12617895-B2

Abstract

A resin composition includes 100 parts by weight of a vinyl group-containing polyphenylene ether resin, 5 parts by weight to 30 parts by weight of a maleimide resin, 5 parts by weight to 40 parts by weight of an active ester and 5 parts by weight to 40 parts by weight of a phosphate ester, wherein the resin composition does not include an epoxy resin. Moreover, also provided is an article made from the resin composition, including a prepreg, a resin film, a laminate or a printed circuit board, and the various properties can be improved including dissipation factor, dissipation factor after thermal aging, dissipation factor variation rate after thermal aging, copper foil peeling strength and alkali resistance.

Inventors

  • XIANG XIONG
  • Zhilong HU
  • Weiliang Chen
  • Yaoqiang MING

Assignees

  • ELITE ELECTRONIC MATERIAL (ZHONGSHAN) CO., LTD.

Dates

Publication Date
20260505
Application Date
20221128
Priority Date
20221025

Claims (12)

  1. 1 . A resin composition, comprising 100 parts by weight of a vinyl group-containing polyphenylene ether resin, 5 parts by weight to 30 parts by weight of a maleimide resin, 5 parts by weight to 40 parts by weight of an active ester and 5 parts by weight to 40 parts by weight of a phosphate ester, wherein the resin composition does not comprise an epoxy resin, and wherein the active ester has a structure as shown below wherein X 1 and X 2 are each independently a phenyl group or a naphthyl group; J 1 , J 2 and J 4 are each independently an unsubstituted arylene group or an substituted arylene group; J 3 is an cycloalkylene group; p and d are each independently 0 or 1; and n is an integer of 1 to 30.
  2. 2 . The resin composition of claim 1 , wherein the vinyl group-containing polyphenylene ether resin comprises a vinylbenzyl group-terminated polyphenylene ether resin, a methacrylate group-terminated polyphenylene ether resin, an allyl group-terminated polyphenylene ether resin or a combination thereof.
  3. 3 . The resin composition of claim 1 , wherein the maleimide resin comprises 4,4′-diphenylmethane bismaleimide, polyphenylmethane maleimide, 2,2′-bis-[4-(4-maleimidephenoxy)phenyl]propane, m-phenylene bismaleimide, bisphenol A diphenyl ether bismaleimide, 3,3′-dimethyl-5,5′-diethyl-4,4′-diphenyl methane bismaleimide, 4-methyl-1,3-phenylene bismaleimide, 1,6-bismaleimide-(2,2,4-trimethyl)hexane, N-2,3-xylylmaleimide, N-2,6-xylylmaleimide, N-phenylmaleimide, maleimide resin containing aliphatic long-chain structure or a combination thereof.
  4. 4 . The resin composition of claim 1 , wherein the phosphate ester comprises resorcinol bis-(diphenyl phosphate), hydroquinone bis-(dixylenyl phosphate), bisphenol A bis-(diphenyl phosphate), resorcinol bis-(dixylenyl phosphate), biphenol bis-(dixylenyl phosphate) or a combination thereof.
  5. 5 . The resin composition of claim 1 , further comprising a maleimide triazine resin, an unsaturated polyolefin resin, a hydrogenated unsaturated polyolefin resin, a small molecule vinyl group-containing resin, a styrene maleic anhydride resin, a phenolic resin, a benzoxazine resin, a cyanate ester resin, a polyamide resin, a polyimide resin or a combination thereof.
  6. 6 . The resin composition of claim 1 , further comprising amine curing agent, inorganic filler, curing accelerator, polymerization inhibitor, coloring agent, solvent, toughening agent, silane coupling agent or a combination thereof.
  7. 7 . An article made from the resin composition of claim 1 , wherein the article comprises a prepreg, a resin film, a laminate, or a printed circuit board.
  8. 8 . The article of claim 7 , having a dissipation factor at 10 GHz as measured by reference to JIS C2565 of less than or equal to 0.00210.
  9. 9 . The article of claim 7 , having a dissipation factor at 10 GHz as measured by reference to JIS C2565 after being subject to 96 hours of aging at 188° C. of less than or equal to 0.00369.
  10. 10 . The article of claim 7 , having a dissipation factor variation rate at 10 GHz as calculated after being subject to 96 hours of aging at 188° C. of less than or equal to 86.53%.
  11. 11 . The article of claim 7 , having a copper foil peeling strength as measured by reference to IPC-TM-650 2.4.8 of greater than or equal to 3.00 lb/in after thermal treatment performed by reference to IPC-TM-650 2.6.27.
  12. 12 . The article of claim 7 , having an alkali resistance as measured from an NaOH alkali resistance test of greater than or equal to 4.0 minutes.

Description

CROSS-REFERENCE TO RELATED APPLICATION This application claims the priority benefits of China Patent Application No. 202211316265.3, filed on Oct. 25, 2022. The entirety the above-mentioned patent application is hereby incorporated by reference herein and made a part of this specification. BACKGROUND 1. Field of the Disclosure The present disclosure mainly relates to a resin composition, more particularly to a resin composition useful for preparing a prepreg, a resin film, a laminate or a printed circuit board. 2. Description of Related Art Recently, the electronic technology has been developed towards higher density, lower power consumption and higher performance, thereby presenting more challenges to the high performance electronic materials. With the intellectualized development of electronic products, the amount of signals that need to be processed is getting larger, and the speed is getting faster. The requirements for signal transmission loss are becoming more and more stringent, especially for 5G base stations and network communication terminals, etc. The high-frequency printed circuit boards (PCBs) used for these equipment rely more and more on copper-clad laminate materials to overcome such problems, which not only presents demands on thermal resistance and electrical properties of the materials, but also presents demands on the performance after thermal aging. Accordingly, inventors have carried out related researches on copper-clad laminate materials. SUMMARY To overcome the problems of prior arts, particularly one or more above-mentioned technical problems facing conventional materials, it is a primary object of the present disclosure to provide a resin composition and an article made therefrom which may overcome at least one of the above-mentioned technical problems. To achieve the above-mentioned object, the present disclosure provides a resin composition, comprising 100 parts by weight of a vinyl group-containing polyphenylene ether resin, 5 parts by weight to 30 parts by weight of a maleimide resin, 5 parts by weight to 40 parts by weight of an active ester and 5 parts by weight to 40 parts by weight of a phosphate ester, wherein the resin composition does not comprise an epoxy resin. For example, in one embodiment, the vinyl group-containing polyphenylene ether resin comprises a vinylbenzyl group-terminated polyphenylene ether resin, a methacrylate group-terminated polyphenylene ether resin, an allyl group-terminated polyphenylene ether resin or a combination thereof. For example, in one embodiment, the maleimide resin comprises 4,4′-diphenylmethane bismaleimide, polyphenylmethane maleimide, 2,2′-bis-[4-(4-maleimidephenoxy)phenyl]propane, m-phenylene bismaleimide, bisphenol A diphenyl ether bismaleimide, 3,3′-dimethyl-5,5′-diethyl-4,4′-diphenyl methane bismaleimide, 4-methyl-1,3-phenylene bismaleimide, 1,6-bismaleimide-(2,2,4-trimethyl)hexane, N-2,3-xylylmaleimide, N-2,6-xylylmaleimide, N-phenyl maleimide, maleimide resin containing aliphatic long-chain structure or a combination thereof. For example, in one embodiment, the active ester has a structure of Formula (I): wherein J1 and J2 each independently comprise an arylene group, and n is an integer of 1 to 30. For example, in one embodiment, the phosphate ester comprises resorcinol bis-(diphenyl phosphate), hydroquinone bis-(dixylenyl phosphate), bisphenol A bis-(diphenyl phosphate), resorcinol bis-(dixylenyl phosphate), biphenol bis-(dixylenyl phosphate) or a combination thereof. For example, in one embodiment, the resin composition further comprises a maleimide triazine resin, an unsaturated polyolefin resin, a hydrogenated unsaturated polyolefin resin, a small molecule vinyl group-containing resin, a styrene maleic anhydride resin, a phenolic resin, a benzoxazine resin, a cyanate ester resin, a polyamide resin, a polyimide resin or a combination thereof. For example, in one embodiment, the resin composition further comprises amine curing agent, inorganic filler, curing accelerator, polymerization inhibitor, coloring agent, solvent, toughening agent, silane coupling agent or a combination thereof. Another main object of the present disclosure is to provide an article made from the aforesaid resin composition, comprising a prepreg, a resin film, a laminate or a printed circuit board. For example, in one embodiment, articles made from the resin composition disclosed herein have one, more or all of the following properties: a dielectric constant at 10 GHz as measured by reference to JIS C2565 of less than or equal to 3.40;a dissipation factor at 10 GHz as measured by reference to JIS C2565 of less than or equal to 0.00210;a dielectric constant at 10 GHz as measured by reference to JIS C2565 after being subject to 96 hours of aging at 188° C. of less than or equal to 3.41;a dissipation factor at 10 GHz as measured by reference to JIS C2565 after being subject to 96 hours of aging at 188° C. of less than or equal to 0.00369;a dielectric cons